Cross Dressing Sissy

By John Nail

Published on Apr 4, 2009

Transgender

I am a straight man a 100% testestrone driven man so this story is kind of out of character for me but I found she was as much if not more of a lady than the women I dated and she was born as a boy. Anyway I just got off work from a farm and ranch supply store in Greybull Wyoming. As I was getting to my pickup a friend of mine came up to me and stopped me by my pickup.

He said," Hey, John what are u doing this weekend?"

I said," I don't know haven't really thought about it."

He said," Look there is a good looking woman that just moved into town and I would have made my moves on her but I have Amy and don't want to mess thing up with her."

I said," Ok so when and where am I supposed to meet this lady?"

He said," You know that house on the corner of 1st Ave? Just go to that house and her name is Jennifer and she is a knockout."

Well around 6:30 pm I pulled up to the house in my pickup it was mud splattered from a flyfishing trip. I was in my best Wranglers my best shirt and my boots were shined and wearing my straw cowboy hat since it was summer. I knocked on her door and I heard Jennifer calling I will be there. She answered the door with a curious look in her face.

Boy Tim was right she is a knock out.

I said," My name is John and my friend Tim told me about you and he said you were new in town and wondering about somebody to go out with."

She said," Tim Bailey you must be that friend he was talking about, you are a handsome man. I would love to go out with you, will you give me a few mins. to change I don't think these sweats are appropiate."

She went into her bedroom and came out wearing this black skirt and suddenly i felt inadaquatly dressed. She asked," Is this good enough?"

I said," You are a knockout Jennifer I can't believe the way I am dressed compared to you."

She laughed and said," Going out with a cowboy is thrilling to me, come on take to a good place for dancing."

Well we went out to my truck and I ran to the right side of my truck and helped her in. I ran over to the left side after closing the door I got in and put the key in the ignition and I smiled at her and said I know a place.

She said," Nice truck where I came from the guys who had pickups used them for everything except what they were originally intended for."

I put the truck in reverse and let out the clutch and backed out of the driveway. into the street.

On the way there I told her about my job at the feed store and how I was born in Greybull and how long I was working at the feed store.

We pulled in front of the dance lounge and saw Tim and Amy in front of the lounge.

Tim said as the women went in," Did I tell you she is hot?"

I said," Yes you did and she is amazing, she told me she came from Chicago and she works at the new computer store here.. She says she came here because she is tired of the big city."

We danced and laughed and before we knew it it was closing time and we ran to the truck like 2 teenagers. I opened the door for her and closed the door and watched her scoot to the middle of the seat. Than I got inside and turned to her and I kissed her and she kissed me back. I drove her to the house and as I was about to go inside she turned and smiled and told me that she didn't sleep with any guy until after dating for about a month. We kissed each other goodnight and I climbed into the truck after waving one final time. On the way home I smiled knowing this was going to be good and knowing I can't wait to see her. Little did I know that night I was going to get the biggest surprise of my life and by the time I would find out I would not care

Next: Chapter 2


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